Sunscreen compositions

ABSTRACT

Novel sunscreen compositions comprising at least one vinylogous amide compound are described as well as methods of protecting the human skin from damaging radiation.

CROSS REFERENCE TO RELATED APPLICATIONS

This is a divisional of application Ser. No. 702,703, filed Feb. 19,1985, now U.S. Pat. No. 4,663,156, which is a continuation-in-part ofapplication Ser. No. 375,072, filed May 5, 1982, now U.S. Pat. No.4,514,383.

BACKGROUND OF THE INVENTION

This invention relates to new and useful ultraviolet radiation sunscreenagents and compositions and to methods of protecting the human skinagainst the potentially harmful effects of sunlight.

It is well documented that human skin is sensitive to sunlightcontaining radiation of wavelengths between about 290 nanometers (nm)and 400 nm as well as artificial light. Ultraviolet radiation ofwavelengths between about 290 nm and 320 nm (UV-B region) has been knownto rapidly produce damaging effects on the skin including reddening orerythema, edema, blistering or other skin eruptions in more severecases. Prolonged or chronic exposure to radiation in this wavelengthrange has been associated with serious skin conditions such as actinickeratoses and carcinomas. In recent years concern has also beenexpressed regarding ultraviolet radiation of wavelengths above 320 nm(UV-A region) and the adverse effects of such radiation on human skin.

In view of the above, protection from the erythemal effects of sunlightproduced by ultraviolet radiation within the UV-B region has been thetraditional objective of sunscreen agents and compositions and as aresult most compounds utilized as sunscreen agents have had lightabsorbance maxima within this UV-B region. Recently, as a result ofgrowing concern for damage to the skin in the UV-A region, compoundscapable of absorbing ultraviolet radiation in this region of thespectrum are becoming increasingly desirable but are generallyunavailable.

Currently, the most widely utilized commercial sunscreen agents includepara-amino benzoic acid derivatives, oxybenzones, methoxycinnamates andsalicylates.

A desirable sunscreen agent should have absorbance maxima in the rangeof between 290 nm and 350 nm; have a molar absorptivity of greater than10,000; be non-toxic, colorless and odorless; be heat and light stable;be water-insoluble and be easily and relatively inexpensively produced.While the readily available commercial sunscreen agents have enjoyed ameasure of success, they all lack one or more of the above desirableproperties.

OBJECTS OF THE INVENTION

It is an object of the present invention to provide improved sunscreenagents and compositions.

It is another object of the present invention to provide sunscreencompositions containing sunscreen agents that overcome the disadvantagesof heretofore available materials and provide adequate and safeprotection for human skin.

It is a further object of this invention to provide methods ofprotecting human skin against the harmful effects of sunlight.

These and other objects and features of the present invention willbecome readily apparent to one skilled in the art from the detaileddescription given hereinafter.

SUMMARY OF THE INVENTION

The foregoing objects and other features and advantages of the presentinvention are achieved by sunscreen compositions containing one or morevinylogous amides as the sunscreen agent.

DETAILED DESCRIPTION OF THE INVENTION

The sunscreen compositions of the present invention contain as an activesunscreen agent at least one vinylogous amide compound of the formula##STR1## wherein R₁ is selected from alkyl, cycloalkyl, alkenyl,cycloalkenyl, aryl, substituted aryl or alkaryl of from 1 to 18 carbonatoms;

R₂ and R₃ may be the same or different and are selected from hydrogen,alkyl, alkenyl, cycloalkyl or cycloalkenyl of from 1 to 18 carbon atoms;

R₄ and R₅ may be the same or different and are selected from hydrogen,alkyl, alkenyl, aryl and substituted aryl, alkaryl, cycloalkyl orcycloalkenyl of from 1 to 18 carbon atoms; provided that at least one ofR₁, R₂, R₃, R₄, or R₅ is interrupted or substituted by N or O. When N ispresent it may be as primary, secondary, or tertiary amine, quaternaryammonium salt, or amide. When O is present it may be as an alcohol,carboxylic acid or ester, or ether. R₂ together with R₁ and/or R₃ mayform carbocyclic and/or heterocyclic rings, and R₄ together with R₅ mayform heterocyclic rings.

The vinylogous amides useful in the present invention can be prepared bymixing equivalent amounts of a suitable amine with a suitableβ-dicarbonyl compound. This may be done without solvent or with anappropriate amount of a solvent such as lower alcohols, toluene, wateror the like. The reaction may require heating, usually at 50° C. to 80°C., for a period of time to complete the reaction.

The vinylogous amides described above include all cis-trans positionalisomers thereof.

Specific examples of vinylogous amides which are useful in the presentinvention include: ##STR2##

The vinylogous amides useful in the formulations of the presentinvention exhibit light absorbance maxima in either the UV-A or UV-Bregions and thus depending on the choice of specific vinylogous amidesone can formulate compositions which are effective sunscreens in eitherof these regions or by selecting a mixture of said vinylogous amides inboth regions of the spectrum. It is also possible and may sometimes bedesirable to combine the vinylogous amide sunscreen agents withconventional sunscreen agents to form effective sunscreen compositions.Such conventional sunscreen agents include Padimate O(2-ethylhexyl-p-dimethylaminobenzoate), oxybenzone, salicylates and thelike.

The sunscreen compositions of the present invention contain thesunscreen agent or combination of sunscreen agents and apharmaceutically extending medium such as a carrier or vehicle whichadapts said agents for application to the skin. These compositions canbe in either solid, liquid or aerosol form. The sunscreen agents of thepresent invention can also be incorporated into various cosmetic andpersonal care products such as hand and body lotions, oils, ointmentslip balm products, facial cosmetics and the like.

The amount of sunscreen agent present in the sunscreen compositions orthe cosmetic and personal care products may vary greatly but ispreferable in a range of about 1 to 20% by weight of the totalcomposition. One or more sunscreen agents may be utilized with thecombined concentration of said agents preferably in the range of 1 to20% by weight of the composition. Greater amounts of these agents may beincorporated into various products limited only by processing andeconomic considerations.

Specific embodiments of the present invention are illustrated by thefollowing examples. It will be understood, however, that the inventionis not confined to the specific limitations set forth in the individualexamples, but rather to the scope of the appended claims.

EXAMPLE I Preparation of Compound (A)

In a suitable reactor equipped with heating, stirring and refluxfacilities are combined under nitrogen atmosphere 100.12 g ofpentane-2,4-dione (1.0 mole), 242.08 of aminoethyl lauramide (1.0 mole)and 500 ml methanol. The mixture is heated at the boil for two hours.Removal of the solvent yields 324 g of a compound of the formula##STR3##

EXAMPLE II Preparation of Compound (C)

In the reactor of Example I are combined 162.0 g of benzoyl acetone (1.0mole), 242.0 g of aminoethyl lauramide (1.0 mole) and 700 ml of toluene.The mixture is heated at 80° C. for one hour. After removal of thesolvent, there remains 386.0 g of a compound of the formula ##STR4##

EXAMPLE III Preparation of Compound (E)

In the reactor of Example I are combined 170.0 g of3-propionyl-2-heptanone (1.0 mole), 61.0 g ethanolamine (1.0 mole) and500 ml methanol. The mixture is heated at the boil for two hours.Removal of the solvent produces 213.0 g of a compound of the formula##STR5##

EXAMPLE IV Preparation of Compound (G)

In a suitable reactor are combined 13.0 g of 1-methoxy-2,4-pentanedione(0.1 mole) and 18.5 g of dodecylamine (0.1 mole). After sufficientheating to melt the reagents, the mixture is heated to 50° C. over a tenminute period. After one hour the mixture cools and yields 29.7 g of acompound of the formula ##STR6##

EXAMPLE V Preparation of Compound (I)

In a suitable reactor are combined 32.4 g of stearoyl acetone (0.1mole), 8.7 g of morpholine (0.1 mole) and 100 ml of methanol. Themixture is heated at the boil for two hours. Removal of the solventproduces a compound of formula ##STR7##

EXAMPLE VI Preparation of Compound (N)

In a suitable reactor are combined 100.12 g of pentane-2,4-dione (1.0mole), 117.0 g of 6-amino-1-hexanol (1.0 mole) and 300 ml of methanol.The mixture is heated at the boil for two hours. Removal of the solventyields 199.0 g of a compound of the formula ##STR8##

EXAMPLE VII Preparation of Compound (O)

19.9 g (0.1 mole) of the product of Example VI in 200 ml of methylenechloride is treated by the gradual addition of 8.4 g (0.1 mole)diketene. When the reaction is complete, 3.1 g of methylamine (0.1 mole)is added and the mixture is heated at the boil for two hours. Removal ofthe solvent yields a compound of the formula ##STR9##

EXAMPLE VIII Preparation of Compound (DD)

In a suitable reactor are combined 100.12 g of pentane-2,4-dione (1.0mole), 75.0 g of glycine (1.0 mole) and 500 ml of water. The mixture isstirred at 60° C. and the pH maintained near 8 until the pH is stable.The mixture is cooled, acidified to pH 3, and evaporated to yield acompound of the formula ##STR10##

EXAMPLE IX Preparation of Compound (HH)

In a suitable reactor are combined 100.12 g of pentane-2,4-dione (1.0mole), 286.0 g of the condensation product of lauric acid withaminoethyl ethanolamine (1.0 mole) and 1000 ml of ethanol. The mixtureis heated at the boil for four hours. Removal of the solvent yields acompound of the formula ##STR11##

EXAMPLE X

A sunscreen formulation is prepared according to the followingprocedure. In a suitable beaker, with vigorous agitation, 1.50 g ofCarbopol 941 thickening agent, 0.25 g disodium ethylenediaminetetraacetate (disodium EDTA) preservative and chelating agent, 1.00 gMethocel K100LV stabilizer and 0.65 g Kathon CG preservative are addedto 354.1 g of deionized water and heated to 70° C. 15.00 g of a 7.5%solution of ammonium hydroxide are added and mixing continues for 5minutes. In a second beaker, 5.00 g stearyl alcohol emollient, 10.00 gEmerest 2400 emollient, 10.00 g mineral oil emollient, 2.50 gdimethicone emollient, 25.00 g Finsolv TN emollient and 15.00 gisostearic acid emulsifier are heated to 70° C. In a third beaker, 25.00g of Compound A and 15.00 g of Compound C are premelted at 70° C. andthen added to the contents in the second beaker and mixed for fiveminutes at 70° C. The contents of the second beaker are then added tothe first beaker and the resulting emulsion is cooled to 50° C.,homogenized, and cooled to room temperature.

The resulting composition is an emulsion which is an opaque, freeflowing lotion.

The resulting composition has the following formulation:

    ______________________________________                                        Ingredient              % by wt.                                              ______________________________________                                        Carbopol 941 (B. F. Goodrich's                                                                        0.30                                                  tradename for carboxy vinyl polymer)                                          disodium EDTA           0.05                                                  Methocel KIOOLV (Dow Chemical's                                                                       0.20                                                  tradename for hydroxypropyl                                                   methylcellulose)                                                              Kathon CG (Rohm & Haas' 0.13                                                  tradename for methyl-and methylchloro-                                        isothiazolinones)                                                             ammonium hydroxide (7.5%)                                                                             3.00                                                  stearyl alcohol         1.00                                                  Emerest 2400 (Emery Industries                                                                        2.00                                                  tradename for glycerol stearate)                                              mineral oil             2.00                                                  isostearic acid         3.00                                                  dimethicone, 50 cs.     0.50                                                  Finsolv TN (Finetex's tradename                                                                       5.00                                                  for C.sub.12 -C.sub.15 alcohol benzoates)                                     Compound A              5.00                                                  Compound C              3.00                                                  deionized water balance to                                                                            100.00                                                ______________________________________                                    

EXAMPLE XI

A sunscreen composition is prepared in accordance with the procedure ofExample X and consists of the following ingredients:

    ______________________________________                                        Ingredient              % by wt.                                              ______________________________________                                        Carbopol 934 (B. F. Goodrich's                                                                        0.30                                                  tradename for carboxy vinyl polymer)                                          disodium EDTA           0.05                                                  Methocel J40MS (Dow Chemical's trade-                                                                 0.50                                                  name for hydroxypropyl methyl-                                                cellulose)                                                                    Kathon CG               0.13                                                  ammonium hydroxide (7.5%)                                                                             3.00                                                  stearyl alcohol         1.00                                                  Emerest 2400            2.00                                                  mineral oil             2.00                                                  isostearic acid         3.00                                                  dimethicone, 50 cs.     0.50                                                  Finsolv TN              5.00                                                  BHT (trade usage for butylated                                                                        0.05                                                  hydroxytoluene)                                                               Compound E              5.00                                                  Compound C              3.00                                                  deionized water balance to                                                                            100.00                                                ______________________________________                                    

The resulting composition is a white, opaque lotion.

EXAMPLE XII

A sunscreen composition is prepared in accordance with the procedure ofExample X and consists of the following ingredients:

    ______________________________________                                        Ingredient          % by wt.                                                  ______________________________________                                        Carbopol 934        0.30                                                      disodium EDTA       0.05                                                      Methocel J40MS      0.50                                                      Kathon CG           0.13                                                      ammonium hydroxide (7.5%)                                                                         3.00                                                      stearyl alcohol     1.00                                                      Emerest 2400        2.00                                                      mineral oil         2.00                                                      isostearic acid     3.00                                                      dimethicone, 50 cs. 0.50                                                      Finsolv TN          5.00                                                      BHT                 0.05                                                      Compound G          5.00                                                      deionized water balance to                                                                        100.00                                                    ______________________________________                                    

The resulting composition is a white, opaque lotion.

EXAMPLE XIII

A sunscreen composition is prepared in accordance with the procedure ofExample X and consists of the following ingredients:

    ______________________________________                                        Ingredient          % by wt.                                                  ______________________________________                                        Carbopol 934        0.30                                                      disodium EDTA       0.05                                                      Methocel J40MS      0.50                                                      Kathon CG           0.13                                                      ammonium hydroxide (7.5%)                                                                         3.00                                                      stearyl alcohol     1.00                                                      Emerest 2400        2.00                                                      mineral oil         2.00                                                      isostearic acid     3.00                                                      dimethicone, 50 cs. 0.50                                                      Finsolv TN          5.00                                                      BHT                 0.05                                                      Compound A          5.00                                                      Padimate O          4.00                                                      deionized water balance to                                                                        100.00                                                    ______________________________________                                    

The resulting composition is a white, opaque lotion.

EXAMPLE XIV

A sunscreen composition is prepared in accordance with the procedure ofExample X and consists of the following ingredients:

    ______________________________________                                        Ingredient          % by wt.                                                  ______________________________________                                        Carbopol 934        0.30                                                      disodium EDTA       0.05                                                      Methocel J40MS      0.50                                                      Kathon CG           0.13                                                      ammonium hydroxide (7.5%)                                                                         3.00                                                      stearyl alcohol     1.00                                                      Emerest 2400        2.00                                                      mineral oil         2.00                                                      isostearic acid     3.00                                                      dimethicone, 50 cs. 0.50                                                      Finsolv TN          5.00                                                      BHT                 0.05                                                      Compound I          7.00                                                      deionized water balance to                                                                        100.00                                                    ______________________________________                                    

The resulting composition is a white, opaque lotion.

EXAMPLE XV

A sunscreen composition is prepared in accordance with the procedure ofExample X and consists of the following ingredients:

    ______________________________________                                        Ingredient          % by wt.                                                  ______________________________________                                        Carbopol 934        0.30                                                      disodium EDTA       0.05                                                      Methocel J40MS      0.50                                                      Kathon CG           0.13                                                      ammonium hydroxide (7.5%)                                                                         3.00                                                      stearyl alcohol     1.00                                                      Emerest 2400        2.00                                                      mineral oil         2.00                                                      isostearic acid     3.00                                                      dimethicone, 50 cs. 0.50                                                      Finsolv TN          5.00                                                      BHT                 0.05                                                      Compound O          8.00                                                      deionized water balance to                                                                        100.00                                                    ______________________________________                                    

The resulting composition is a white, opaque lotion.

EXAMPLE XVI

A sunscreen composition is prepared in accordance with the procedure ofExample X and consists of the following ingredients:

    ______________________________________                                        Ingredient          % by wt.                                                  ______________________________________                                        Carbopol 934        0.30                                                      disodium EDTA       0.05                                                      Methocel J40MS      0.50                                                      Kathon CG           0.13                                                      ammonium hydroxide (7.5%)                                                                         3.00                                                      stearyl alcohol     1.00                                                      Emerest 2400        2.00                                                      mineral oil         2.00                                                      isostearic acid     3.00                                                      dimethicone, 50 cs. 0.50                                                      Finsolv TN          5.00                                                      BHT                 0.05                                                      Compound HH         5.00                                                      Padimate O          3.00                                                      deionized water balance to                                                                        100.00                                                    ______________________________________                                    

The resulting composition is a white, opaque lotion.

EXAMPLE XVII

A hand and body lotion composition is prepared as follows:

In a suitable beaker with vigorous agitation, 3.0 g of Carbopol 934 and40 g propylene glycol are added to 788.7 g deionized water and heated to70° C. In a second beaker, 10 g isopropylpalmitate, 10.0 g dimethicone(50 cs), 12.5 g oleic acid, 10.0 g stearoxymethylsilane, 8.0 g sorbitanstearate, 5.0 g cetyl alcohol, 5.0 g stearyl alcohol, 5.0 g syntheticbeeswax, 12.5 g glyceryl monostearate, 12.5 g stearic acid, 12.0 gpolysorbate 61, 15.0 g myristyl myristate, 2.0 g BHT and 3.0 g benzylalcohol are melted. The contents of the second beaker are added to thecontents of the first beaker and to the resultant mixture are added 0.5g butylparaben, 1.0 g propylparaben and 1.5 g methylparaben followed bythe addition of 2.6 g of a 50% solution of sodium hydroxide, 20.0 g ofCompound A and 20.0 g of Compound C. The resulting emulsion ishomogenized and cooled to 45° C. at which point 2.0 g of fragrance areadded followed by cooling to room temperature resulting in a thick,white lotion.

The resulting composition has the following formulation:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        Carbopol 934       0.30                                                       propylene glycol   4.00                                                       isopropyl palmitate                                                                              1.00                                                       dimethicone, 50 cs.                                                                              1.00                                                       oleic acid         1.25                                                       stearoxymethylsilane                                                                             1.00                                                       sorbitan stearate  0.80                                                       cetyl alcohol      0.50                                                       stearyl alcohol    0.50                                                       synthetic beeswax  0.50                                                       glyceryl monostearate                                                                            1.25                                                       stearic acid       1.25                                                       polysorbate 61     1.20                                                       myristyl myristate 1.50                                                       butylparaben       0.05                                                       propylparaben      0.10                                                       methylparaben      0.15                                                       BHT                0.02                                                       sodium hydroxide (50%)                                                                           0.26                                                       benzyl alcohol     0.30                                                       fragrance          0.20                                                       Compound A         2.00                                                       Compound C         2.00                                                       deionized water balance to                                                                       100.00                                                     ______________________________________                                    

EXAMPLE XVIII

A lotion formulation is prepared according to the procedure of ExampleXVII and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        Carbopol 934       0.30                                                       propylene glycol   4.00                                                       isopropyl palmitate                                                                              1.00                                                       dimethicone, 50 cs.                                                                              1.00                                                       oleic acid         1.25                                                       stearoxymethylsilane                                                                             1.00                                                       sorbitan stearate  0.80                                                       cetyl alcohol      0.50                                                       stearyl alcohol    0.50                                                       synthetic beeswax  0.50                                                       glyceryl monostearate                                                                            1.25                                                       stearic acid       1.25                                                       polysorbate 61     1.20                                                       myristyl myristate 1.50                                                       butylparaben       0.05                                                       propylparaben      0.10                                                       methylparaben      0.15                                                       BHT                0.02                                                       sodium hydroxide (50%)                                                                           0.26                                                       benzyl alcohol     0.30                                                       fragrance          0.20                                                       Padimate O         4.00                                                       Compound C         3.00                                                       deionized water balance to                                                                       100.00                                                     ______________________________________                                    

The resulting composition is a thick, white lotion.

EXAMPLE XIX

A lotion formulation is prepared according to the procedure of ExampleXVII and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        Carbopol 934       0.30                                                       propylene glycol   4.00                                                       isopropyl palmitate                                                                              1.00                                                       dimethicone, 50 cs.                                                                              1.00                                                       oleic acid         1.25                                                       stearoxymethylsilane                                                                             1.00                                                       sorbitan stearate  0.80                                                       cetyl alcohol      0.50                                                       stearyl alcohol    0.50                                                       synthetic beeswax  0.50                                                       glyceryl monostearate                                                                            1.25                                                       stearic acid       1.25                                                       polysorbate 61     1.20                                                       myristyl myristate 1.50                                                       butylparaben       0.05                                                       propylparaben      0.10                                                       methylparaben      0.15                                                       BHT                0.02                                                       sodium hydroxide (50%)                                                                           0.26                                                       benzyl alcohol     0.30                                                       fragrance          0.20                                                       octyl salicylate   2.00                                                       Compound E         2.00                                                       deionized water balance to                                                                       100.00                                                     ______________________________________                                    

The resulting composition is a thick, white lotion.

EXAMPLE XX

A lotion formulation is prepared according to the procedure of ExampleXVII and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        Carbopol 934       0.30                                                       propylene glycol   4.00                                                       isopropyl palmitate                                                                              1.00                                                       dimethicone, 50 cs.                                                                              1.00                                                       oleic acid         1.25                                                       stearoxymethylsilane                                                                             1.00                                                       sorbitan stearate  0.80                                                       cetyl alcohol      0.50                                                       stearyl alcohol    0.50                                                       synthetic beeswax  0.50                                                       glyceryl monostearate                                                                            1.25                                                       stearic acid       1.25                                                       polysorbate 61     1.20                                                       butylparaben       0.05                                                       propylparaben      0.10                                                       methylparaben      0.15                                                       BHT                0.02                                                       sodium hydroxide (50%)                                                                           0.26                                                       benzyl alcohol     0.30                                                       fragrance          0.20                                                       Compound O         4.00                                                       deionized water balance to                                                                       100.00                                                     ______________________________________                                    

The resulting composition is a thick, white lotion.

EXAMPLE XXI

A lotion formulation is prepared according to the procedure of ExampleXVII and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        Carbopol 934       0.30                                                       propylene glycol   4.00                                                       isopropyl palmitate                                                                              1.00                                                       dimethicone, 50 cs.                                                                              1.00                                                       oleic acid         1.25                                                       stearoxymethylsilane                                                                             1.00                                                       sorbitan stearate  0.80                                                       cetyl alcohol      0.50                                                       stearyl alcohol    0.50                                                       synthetic beeswax  0.50                                                       glyceryl monostearate                                                                            1.25                                                       stearic acid       1.25                                                       polysorbate 61     1.20                                                       butylparaben       0.05                                                       propylparaben      0.10                                                       methylparaben      0.15                                                       BHT                0.02                                                       sodium hydroxide (50%)                                                                           0.26                                                       benzyl alcohol     0.30                                                       fragrance          0.20                                                       Compound I         2.00                                                       Compound DD        2.00                                                       deionized water balance to                                                                       100.00                                                     ______________________________________                                    

The resulting composition is a thick, white lotion.

EXAMPLE XXII

A hand cream composition is prepared according to the followingprocedure. In a suitable beaker 367.4 g mineral oil, 55.0 g lanolin,80.0 g white wax, 45.7 g paraffin, 70.0 g synthetic beeswax, 10.0 gglyceryl monostearate and 68.5 g white ceresine wax are melted and keptat a temperature of 70° C. In a second beaker 241.8 g of deionizedwater, 9.0 g powdered borax and 1.0 g propylparaben are heated to 70° C.and the contents of the first beaker are added to the second beaker and30 g of Compound A and 20.0 g of Compound C are added thereto. Themixture is cooled to 55° C. and 1.6 g of fragrance are added and thecooling continued to 45° C. and the resulting composition filled in asuitable container and cooled to room temperature.

The resulting composition has the following formulation:

    ______________________________________                                        Ingredients          % by wt.                                                 ______________________________________                                        mineral oil          36.74                                                    lanolin, anhydrous cosmetic grade                                                                  5.50                                                     white wax, USP       8.00                                                     paraffin             4.57                                                     synthetic beeswax    7.00                                                     glyceryl monostearate                                                                              1.00                                                     white ceresine wax   6.85                                                     powdered borax       0.90                                                     fragrance            0.16                                                     propylparaben        0.10                                                     Compound A           3.00                                                     Compound C           2.00                                                     deionized water      balance to 100.00                                        ______________________________________                                    

EXAMPLE XXIII

A hand cream formulation is prepared according to the procedure ofExample XXII and consists of the following ingredients:

    ______________________________________                                        Ingredients          % by wt.                                                 ______________________________________                                        mineral oil          36.74                                                    lanolin, anhydrous cosmetic grade                                                                  5.50                                                     white wax, USP       8.00                                                     paraffin             4.57                                                     synthetic beeswax    7.00                                                     glyceryl monostearate                                                                              1.00                                                     white ceresine wax   6.85                                                     powdered borax       0.90                                                     fragrance            0.16                                                     propylparaben        0.10                                                     Compound AA          3.00                                                     deionized water      balance to 100.00                                        ______________________________________                                    

EXAMPLE XIV

A hand cream formulation is prepared according to the procedure ofExample XXII and consists of the following ingredients:

    ______________________________________                                        Ingredients          % by wt.                                                 ______________________________________                                        mineral oil          36.74                                                    lanolin, anhydrous cosmetic grade                                                                  5.50                                                     white wax, USP       8.00                                                     paraffin             4.57                                                     synthetic beeswax    7.00                                                     glyceryl monostearate                                                                              1.00                                                     white ceresine wax   6.85                                                     powdered borax       0.90                                                     fragrance            0.16                                                     propylparaben        0.10                                                     Compound O           3.00                                                     deionized water      balance to 100.00                                        ______________________________________                                    

EXAMPLE XXV

A hand cream formulation is prepared according to the procedure ofExample XXII and consists of the following ingredients:

    ______________________________________                                        Ingredients          % by wt.                                                 ______________________________________                                        mineral oil          36.74                                                    lanolin, anhydrous cosmetic grade                                                                  5.50                                                     white wax, USP       8.00                                                     paraffin             4.57                                                     synthetic beeswax    7.00                                                     glyceryl monostearate                                                                              1.00                                                     white ceresine wax   6.85                                                     powdered borax       0.90                                                     fragrance            0.16                                                     propylparaben        0.10                                                     octyl salicylate     4.00                                                     Compound R           3.00                                                     deionized water      balance to 100.00                                        ______________________________________                                    

EXAMPLE XXVI

A hand cream formulation is prepared according to the procedure ofExample XXII and consists of the following ingredients:

    ______________________________________                                        Ingredients          % by wt.                                                 ______________________________________                                        mineral oil          36.74                                                    lanolin, anhydrous cosmetic grade                                                                  5.50                                                     white wax, USP       8.00                                                     paraffin             4.57                                                     synthetic beeswax    7.00                                                     glyceryl monostearate                                                                              1.00                                                     white ceresine wax   6.85                                                     powdered borax       0.90                                                     fragrance            0.16                                                     propylparaben        0.10                                                     Compound JJ          2.00                                                     deionized water      balance to 100.00                                        ______________________________________                                    

EXAMPLE XXVII

A dry skin composition is prepared in accordance with the followingprocedure. In a suitable beaker 450.0 g petrolatum, 30.0 g polyethyleneand 20.0 g silicon dioxide are melted at 80° C. and homogenized. To thismixture, 338.0 g cyclomethicone, 100.0 g dimethicone, 10.0 g mineraloil, 1.0 g propylparaben, 1.0 g sorbic acid and 50.0 g Compound Q areadded and the resultant mixture is cooled to 35° C.

The resulting composition has the following formulation:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        petrolatum, white USP                                                                            45.0                                                       polyethylene       3.0                                                        silicon dioxide    2.0                                                        cyclomethicone     33.8                                                       dimethicone, 50 cs.                                                                              10.0                                                       mineral oil        1.0                                                        propylparaben      0.1                                                        sorbic acid        0.1                                                        Compound O         5.0                                                                           100.0                                                      ______________________________________                                    

EXAMPLE XVIII

A dry skin formulation is prepared according to the procedure of ExampleXXVII and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        petrolatum, white USP                                                                            49.0                                                       polyethylene       3.0                                                        silicon dioxide    2.0                                                        cyclomethicone     33.8                                                       dimethicone, 50 cs.                                                                              10.0                                                       mineral oil        1.0                                                        propylparaben      0.1                                                        sorbic acid        0.1                                                        Compound MM        5.0                                                                           100.0                                                      ______________________________________                                    

EXAMPLE XXIX

A dry skin formulation is prepared according to the procedure of ExampleXXVII and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        petrolatum, white USP                                                                            45.0                                                       polyethylene       3.0                                                        silicon dioxide    2.0                                                        cyclomethicone     33.8                                                       dimethicone, 50 cs.                                                                              10.0                                                       mineral oil, J & J Special                                                                       1.0                                                        propylparaben      0.1                                                        sorbic acid        0.1                                                        Padimate O         3.0                                                        Compound C         2.0                                                                           100.0                                                      ______________________________________                                    

EXAMPLE XXX

A dry skin formulation is prepared according to the procedure of ExampleXXVII and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        petrolatum, white USP                                                                            45.0                                                       polyethylene       3.0                                                        silicon dioxide    2.0                                                        cyclomethicone     33.8                                                       dimethicone, 50 cs.                                                                              10.0                                                       mineral oil        1.0                                                        propylparaben      0.1                                                        sorbic acid        0.1                                                        oxybenzone         2.0                                                        Compound B         3.0                                                                           100.0                                                      ______________________________________                                    

EXAMPLE XXXI

A lip balm composition is prepared according to the following procedure.In a suitable beaker 72.0 g petrolatum, 8.0 g Syncrowax HRC, 8.0 gSyncrowax ERL-C, 8.0 g Syncrowax HGL-C, 2.0 g Compound B and 2.0 goxybenzone are added. The mixture is melted and cast into sticks at atemperature of 60° C.

The resulting composition has the following formulation:

    ______________________________________                                        Ingredients              % by wt.                                             ______________________________________                                        petrolatum, white USP    72.0                                                 Syncrowax HRC (Croda's tradename for                                                                   8.0                                                  glyceryl tribehenate)                                                         Syncrowax ERL-C (Croda's tradename for                                                                 8.0                                                  C.sub.18 -C.sub.36 wax fatty acid-                                            ethylene glycol ester)                                                        Syncrowax HGL-C (Croda's tradename for                                                                 8.0                                                  C.sub.18 -C.sub.36 wax fatty acid triglyceride)                               Compound B               2.0                                                  oxybenzone               2.0                                                                           100.0                                                ______________________________________                                    

EXAMPLE XXXII

A lip balm composition is prepared according to the procedure of ExampleXXXI and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        petrolatum, white USP                                                                            69.0                                                       Syncrowax HRC      8.0                                                        Syncrowax ERL-C    8.0                                                        Syncrowax HGL-C    8.0                                                        Compound A         4.0                                                        Compound C         3.0                                                                           100.0                                                      ______________________________________                                    

EXAMPLE XXXIII

A lip balm composition is prepared according to the procedure of ExampleXXXI and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        petrolatum, white USP                                                                            70.0                                                       Syncrowax HRC      8.0                                                        Syncrowax ERL-C    8.0                                                        Syncrowax HGL-C    8.0                                                        Compound M         2.0                                                        Padimate O         4.0                                                                           100.0                                                      ______________________________________                                    

EXAMPLE XXXIV

A lip balm composition is prepared according to the procedure of ExampleXXXI and consists of the following ingredients:

    ______________________________________                                        Ingredients        % by wt.                                                   ______________________________________                                        petrolatum, white USP                                                                            74.0                                                       Syncrowax HRC      8.0                                                        Syncrowax ERL-C    8.0                                                        Syncrowax HGL-C    8.0                                                        octyl salicylate   1.0                                                        Compound HH        1.0                                                                           100.0                                                      ______________________________________                                    

What is claimed is:
 1. A sunscreen composition comprising an extendingmedium and from about 1 to 20% by weight of the total composition of atleast one vinylogous amide compound of the formula ##STR12## wherein R₁is selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl,substituted aryl or alkaryl of from 1 to 18 carbon atoms;R₂ and R₃ arethe same or different and are selected from hydrogen, alkyl, alkenyl,cycloalkyl or cycloalkenyl of from 1 to 18 carbon atoms; R₄ and R₅ arethe same or different and are selected from hydrogen, alkyl, alkenyl,aryl and substituted aryl, alkaryl, cycloalkyl or cycloalkenyl of from 1to 18 carbon atoms; provided that at least one of R₄ or R₅ isinterrupted or substituted by N; wherein N is selected from the groupconsisting of primary amines, secondary amines, tertiary amines, andquaternary ammonium salts; and furthermore wherein R₂ together with R₁and/or R₃ may form carbocyclic rings and R₄ together with R₅ may formheterocyclic rings.
 2. The composition of claim 1 wherein the vinylogousamide is of the formula ##STR13##
 3. The composition of claim 1containing at least one vinylogous amide and in addition oxybenzone. 4.The composition of claim 1 containing at least one vinylogous amide andin addition 2-ethylhexyl-p-dimethylaminobenzoate.
 5. The composition ofclaim 1 containing the vinylogous amide is of the formula ##STR14## 6.The composition of claim 1 wherein the vinylogous amide is of theformula ##STR15##
 7. The composition of claim 1 wherein the vinylogousamide is of the formula ##STR16##
 8. The composition of claim 1 whereinthe vinylogous amide is of the formula ##STR17##
 9. The composition ofclaim 1 wherein the vinylogous amide is of the formula ##STR18##
 10. Amethod of protecting human skin from the erythmic effects of ultravioletradiation which comprises applying to the skin a sunscreen compositioncontaining an extending medium and from about 1 to 20% by weight of thetotal composition of at least one vinylogous amide compound of theformula ##STR19## wherein R₁ is selected from alkyl, cycloalkyl,alkenyl, cycloalkenyl, aryl, substituted aryl or alkaryl of from 1 to 18carbon atoms;R₂ and R₃ are the same or different and are selected fromhydrogen, alkyl, alkenyl, cycloalkyl or cycloalkenyl of from 1 to 18carbon atoms; R₄ and R₅ are the same or different and are selected fromhydrogen, alkyl, alkenyl, aryl and substituted aryl, alkaryl, cycloalkylor cycloalkenyl of from 1 to 18 carbon atoms; provided that at least oneof R₄ or R₅ is interrupted or substituted by N; wherein N is selectedfrom the group consisting of primary amines, secondary amines, tertiaryamines, and quaternary ammonium salts and furthermore wherein R₂together with R₁ and/or R₃ may form carbocyclic rings and R₄ togetherwith R₅ may form heterocyclic rings.